Pros and Cons
by v4rtij4ton
Summary: Damian decides he needs to find Dick a suitable partner to date, since it's obvious Dick cannot be trusted with such a task himself. And he recruits Jason (obvious choice?) to help him. Result isn't quite what Damian had hoped for, but it's love what matters right? JayDick.
1. Chapter 1

**This is my very first Batman fanfic, which didn't actually take too long to write and I'm really excited for this, I enjoyed writing it. So please lemme know what you think, and I hope you enjoy this as much as I enjoyed doing it.**

 **Warnings consist of Jason's foul mouth...**

 **I don't own Batman, or any other characters.**

 _-Meeting at Larry's waffle house - 5pm sharp, don't be late_

Jason breathed out the smoke from his lungs, watching the window of the shop across the street, he took the moment to think once more whether he should simply walk away, get the fuck out of the place - let the demon brat do whatever he wished, or if he should walk in to find out what was going on. It wasn't as if Damian Wayne usually sent him messages willingly, actually, the brat probably wouldn't send anything this... borderline kind even if he'd be threatened by a gun. So that was all the reason why he was standing across the street to the meeting place, already five minutes late - just to piss off the brat of Wayne manor. Jason wanted to know why the demon brat wanted to meet him, there was no one else around, so this didn't seem like a plan to take him down.

And Jason had expected to see Dick loitering around, his second guess - after it being a possible trap to drag Jason's sorry -but sexy- ass into Arkham asylum, had been to assume this was Dick's plan of bringing them all together for ice cream, or some sort of other crap what the elder male liked to do. However Nightwing wasn't here…

Jason refused to feel slightly disappointed by that fact.

"Tch", the cigarette butt was flicked off and he stomped on it, the sooner he'd walk in the sooner he'd know what the brat had on his mind. Sure they said curiosity killed the cat, but since Jason had already died - what did he have to lose? And with this newfound determination he headed for the door, crossing the street only to have cars honk at him and a biker curse at him - to which Jason responded by sticking a finger up for the man, before he was at the door. The all too familiar jingle of a bell over the door, and Jason did a quick sweep of the place before his eyes landed on Damian.

Oh Jason couldn't (didn't even try) to contain the grin splitting his lips as he stalked over, the demon brat sitting in a ice cream shop, drinking his weirdass tea and glaring holes to anyone who came close, including Jason. It was too funny to be taken seriously! And the brat was alone, this was going to be interesting. "Hey tator-tot, Dick not take you to ice cream lately? You coulda just asked him", the glare just intensified and Jason was sure if looks could've killed he'd have been dead, but then again, everyone around Damian would've been dead a long time ago.

"Todd, you're late. I gave you simple instructions to follow", Jason pulled himself a chair across the table shrugging his shoulders, he really didn't care, which the Robin was able to figure out as after a slight growl he let out a breathe, which seemed to be something to calm him down, to help him to deal with Jason. So... why was the pipsqueak making himself through this suffering?

"What are we here for? If not ice cream. And if we are here for ice cream you do realise Dick is going to do that kicked puppy regime since you didn't invite him along"

"I need your assistance to find a suitable partner for Grayson", that rendered Jason silent, suitable partner for Dick? Dick had never had any problems finding a partner, he had all the women and men swooning after that ass, which Jason admitted was one fine ass. Hell the second Robin still had wet dreams of it, he had been having wet dreams of Dick's nice ass when he had met the man, Jason approved that ass. It was just a shame he never got too close to it, something to do with waving his guns every time they met? But why would Damian need or want to get himself dragged into this business? Did the brat even know what a 'partner' meant?

Oh dear god, Jason was NOT going to give THE SPEECH to the demon brat, that was Bruce's job.

"Stop gaping Todd, makes you look even more stupid", sure enough Jason snapped his mouth shut, leaning his elbows on the table, he would entertain the brat, okay he would entertain himself, because this sounded hilarious. And possibly something he could use to mess with Bruce, and Dick's lovelife, which he would love to do both.

"Why would you want to find Dickie a partner? He has plenty and he doesn't have problems with finding partners. Also what do you need me for? Go to Replacement", Damian looked at him like he was stupid, and useless, but that's how Damian always looked at him. Hell, Jason was pretty sure no one but Dick could get any other emotion out of this kid, and with emotion he meant, less angry and less stabbity stab stab kind of actions.

"Drake is even more useless than you. And you seem to speak with Grayson about these issues, so you can give an insight to what are HIS preferences", why did Jason get a feeling Dick's preferences didn't matter when the demon was setting him up with someone? "His last relationship left him an emotional mess, again, and when he gets like that he becomes overly clingy and needs us to spend time with him. Also he is too kind for his own good, so he needs others to make this decision for him - I will make a rational decision whom he should date and settle down with since he is unable to make such a choice, which would work in the long run and not hinder with our work", Jason tried not to grin, failing miserably again, this was too good. The demon brat really seemed to believe in his plan of getting Dick to date someone based on what the brat thought would be good. Would this entail Dick dating an assassin or the cute girl selling the ice cream?

"I've already gone through possible candidates", the brat pulled out a tablet, opening an excel file, AN EXCEL FILE, of the possible people he could consider letting Dick date, Jason was quick to snatch it off his hands, rather surprised to see both men and female on the list, it was impressive. The demon brat was going to quite the lengths to get Dick a proper partner. Damian glared at him for taking the tablet off him but he said nothing about it, instead he calmly took a sip of his tea, gauging Jason for a reaction.

"So... what is the next step?"

"You will find out Graysons opinions on the candidates and then we will set up dates, where I can find out if it is going to work or not. And you will find out if the chemistry is there", the brat had been thinking about everything, Jason's eyes scanned the names on the list, the brat had done extensive background checks on everyone, there was pros and cons listed, there was possible marks on which could get Dick's attention... this shit was creepy.

But honestly, Damian had a point, the brat wasn't... right, but he had a good point. Dick did usually go in and out of relationships rather fast, the man thought too much with his emotions rather than making rational decisions with his mind. Dick had sometimes mentioned something of his relationships to Jason, they never spoke too... deeply about emotions, but Jason could not miss the fact every time Dick had his heart broken he became touchy and feely. Jason didn't complain, he DID NOT need physical closeness, but Dick was nice to touch and feel. Like really fucking nice, nice enough to push down and have his way with him, he was going to jack off on that thought tonight.

"Alright, let the mission Get Dick some dick begin!" Jason could feel the appalled looks from the adults around on his back, oh was he too loud? Demon brat however just scowled, but looked somewhat satisfied as he plucked the tablet off Jason's hold. Damian really couldn't fathom why his father had brought these people into the house, they were all good for nothing.

"I will message you the details, meanwhile - be useful and find a place where to hold these dates so we can keep an eye on Grayson", Jason snorted, this was like planning on looking after fifteen year old on the first hormone filled date, was Damian ready to see what his precious elder brother did with women, and men. Not that the brat gave him the chance to ask, he was up and out of the place, followed by the jingle of the bell on the door, which caused Jason snigger once more, demon brat in an ice cream shop, hilarious! And while he was there, he might as well get a scoop or five. Because when you were a responsible adult you could have ice cream for dinner!


	2. Chapter 2

**Time to bring the party boy into the party. I feel Damian is bad at the whole dating game, so if anyone has suggestions on where and what kind dates there should be lemme know! I'm open for all suggestions.**

 **I don't own Batman or any other characters**

Usually when, if, Dick got a call from one of his brothers to meet up for a relaxed evening together, the acrobat jumped at the chance. It wasn't often when his brothers would be the ones reaching out to him, to get together and be able to spend some time together. So whenever it did happen, when Jason called him in the middle of beating down some lowlives causing troubles in Blüdhaven, Dick was surprised, pleasantly so, and he would shift around his plans and schedule in order to be able to go and see his little brothers. It was a treat he rarely had time for nowadays, shame really.

But this time when he saw Jason's name on the ID of his phone screen the eldest Robin just wanted to ignore it. And Jason was calling him right as he had been able to sneak back into his own apartment, as crazy as it sounded, Dick didn't know anyone else who'd have to sneak into their very own apartment at 3am to catch four maybe five hours of sleep before running off to be a cop. A cop sneaking into their own apartment, that'd make headlines, Dick had to snigger at his own thoughts. He was way too tired for this. However Dick did always answer to his brothers, who knew, it could've been an emergency and he wouldn't have been able to live with himself if he had not answered and something grave would've happened. He lived with those nightmares sometimes, and since this was Jason, all the more reason to assume the man was bleeding out somewhere in the back alley. Unfortunately when he managed to struggle his Nightwing suit half way off, and he got his phone to his ear, his words were just a mumbled mess.

"You want me to what Dickie?" Jason's voice was amused in the phone and Dick groaned slightly, not so kindly kicking the rest of the suit off and putting it away, he barely remembered to get his mask off before he landed on the bed, with a slight oomph, the bed had never felt so nice under him. So soft and comfortable. He had been too busy, he had been working non stop, day and night. Of course he was used to it but, it had been going on for a while now and Dick was looking forward to sleeping 24 hours straight, preferably longer, however the bad guys weren't really giving him slack. Maybe he should call Timmy to ask for some tips on how to stay awake for the rest of the week too.

"Jason, as nice as it is to hear from you, I really want to sleep right now. So... can we talk later?" Dick didn't even try to hide the hopeful tone in his voice. He was too tired to feel apologetic for the fact he didn't want to talk to someone.

"I'm throwing a party in Gotham, and you're invited, other birds will be attending too, so you better join us. Good old times, just with less ass kicking and more whiskey", Nightwing bit back a groan, of course, play into his weakness, he missed his brothers and he wouldn't say no to a chance of spending a night with all of them. And of course, he was tired, he was close to agreeing to anything if he just got to go to sleep. They both knew the game was won by Jason already, and Dick was kind of falling asleep already.

"Alright, anything you say Jaybird, just... send details, I need to sleep now", his words were barely coherent enough for Jason to be able to make out what he was saying. Dick heard a chuckle from the other end of the phone, made him smile, made his heart flutter a bit. Oh he was stupid and he was the worst, but something about Jason smiling and being relaxed made the world seem like so much more brighter place, it would be nice to see Jason, and Damian and Tim too, so maybe this wouldn't be such a bad thing, such a bad call to take.

"Sweet dreams Dickiebird", now wasn't that a sweet thing from someone who put bullets into people?

What Jason had imagined was that they'd be holding separate dates for these candidates Damian had picked out for Dick, get to go through them one by one, see what Dick liked, or what worked, Jason was still convinced Damian didn't actually care what Dick thought, as long as the relationship would work. So that Dick wouldn't get hurt and end up as a mess, sure the demon brat told him he was doing it so that they wouldn't need to deal with the mess it'd cause, but Jason knew better. Somewhere deep down Damian cared, and wanted to keep Dick safe, and happy, everyone else could drop dead and disappear. That had become clear once more when they had been setting up this... group date. Only Dick mattered.

Of course Jason had sold it to Dick as a night to spend time together, but really, it was a group date. And the Red Hood would have to remember to have some words with Alfred, Damian's time on the TV had to be cut down, Jason was sure by now this all had started off from something like Bachelor, or worse Temptation Island, and he wasn't really sure if he wanted to know where this was going. But the night was young, they were using Bruce's penthouse in the city for the whole party thing, and there was... plenty of offerings, music, food (Jason had been adamant on food), everything was in order.

On top of all just to annoy the pipsqueak Jason had also invited Tim to come along, the detective didn't need to know what they had planned, or what the party was for. Jason was sure Tim was able to figure it out, but he didn't really care, Jason wasn't completely sure this plan would work anyhow. And honestly, he had told Dick the Robins would be there so, he had made sure all Robins would be there!

Now that it was all going smoothly, much for Jason's delight Damian was swarmed by all the women swooning over him, annoying the demon to no end, it was only waiting game for the man of the night to arrive. Jason was busy stuffing his face with the sweet delicacies Alfred had arranged, Jason never denied his sweet tooth when he happened to get the chance to enjoy some sugar in the best forms possible. And Dick was late, which wasn't really unusual, the man was about as organised as a tornado. Jason was already thinking the man had stood them up, maybe being too busy being a vigilante, which was only normality in their lives. When the door to the penthouse opened and the man of the hour walked in, clearly surprised by the amount of people in the house, but the shock was quickly replaced by a smile when Tim rushed to greet the man. Jason stuffed one more mini cupcake into his mouth before getting up and walking over too.

"Dickiebird! Was starting to think something had eaten you up", he grinned for the man, and Jason noticed how tired the man looked, but Dick still smiled, giving a shrug, and that look, that damned look, a little bit from under his bangs, looking like a pup who needed some love. Jason gave a sigh, opening his arms a bit; "fine", Dick's face lit up in a smile and it was less than a second when Jason's arms were full of Nightwing, hugging the living daylights out of him. Jason wasn't much for touching, but he had to admit, Dick had taught him to like these hugs, so maybe he enjoyed them a bit. However he was a scary vigilante, he couldn't tell that to anyone! So when Dick took a step back Jason went to give a roll of his eyes at the man, Dick didn't buy it, of course.

"Was there problems?" Tim broke the silent argument, getting a sigh from Dick in return and the man ran a hand through his hair, Jason made a note again how tired the man looked when he let the smile falter a bit. Dick had said in the phone he just wanted to sleep, maybe he would've been a better brother if he hadn't asked the man over.

"Would you believe the bad guys don't want me to have a night off?" Jason was very aware of that issue. No one told about it in the Vigilante handbook though, they only spoke about doing good and saving lives, not about the fact you'd need to give up sex life and family, drinking and partying were also gone the moment you gained some enemies in the field.

"Don't fret, tonight is all about you, time to let loose!" oh Dick didn't know how much this was about him, and Jason's words brought back the smile on the man's face.

"Grayson! You're late, was there troubles on the way?" Damian stomped his way over, arms crossed over his chest, looking less than impressed, and... a bit red, which was from either embarrassment or anger, or both. Jason was pretty sure more of the latter, but hey this had been all of the Damian's idea, so the brat suffered because of his own plan, and he deserved all of it if one asked Jason. Dick ignored it, smiling for Damian too, and despite the boy's protests he went to hug him as well, trained eye noticed Damian didn't actually try as hard as he could to fight the hug. Only slightly sorting out his clothes when Dick "unhanded" him.

"Are we done with this now? I have people you need to meet and talk to", the demand was quite off, so much for being smooth and discreet, but since all of them knew Damian rarely if ever made much sense to a normal person, Dick bought how Jason and Tim just shrugged their shoulders to his questioning stare and let the Robin guide him through to the crowd, introducing him to the people he had found good enough for the first round of Lets-get-Dick-some-dick plan. Jason almost felt sorry, but the confusion on Dick's face was priceless, well worth all of the work they had put into this. Jason could tell Tim wanted to inquire more, he was curious by birth, the detective, but it looked like this time he didn't want to know, not yet anyway - if ever, sometimes it was better to not know everything. Especially if Damian was involved.

Jason could say night was going smoothly after it, he settled back to catering to his sweet cravings, watching from distance as Dick met all of these people, Damian was taking him out around, having him say hi to everyone, leaving him to talk with them. And Jason found himself picking flaws in the men and women, why they shouldn't be with Dick, it was very unhealthy of course, he should've been there to help Damian pick which one of these guys was good for Dick, help Damian find the man the right person to date. But none of these people were good enough, Jason growled at his own thoughts, how many people were here just to try and get into the good money Dick had because of Bruce. That was always too real chance to happen, there was always people around who only wanted money.

So, he didn't approve any of these people, and maybe he was a bit... annoyed (jealous- but he'd never admit that) of the fact Dick was spending all this time with strangers, when it had been ages since Jason saw the man and Dick should've spent this time bonding with him instead. Fuck what was he? A hormonal teenager?

Jason didn't even really remember his part of the whole deal until Damian approached him, bothering him to go and find out what Dick thought of the people, Jason didn't need to know, but he didn't want to be nagged by the demon brat so in the end he ended up going to track down Nightwing, finding the man sitting alone in the study Bruce had in the apartment. Surprisingly the man was startled by the sound of someone coming in, turning to look at Jason, obviously going to apologise from missing from the party - to some of the guests or maybe Damian- but as he saw it was Jason he relaxed, giving a weary smile.

"When you said party I was thinking more of... bad movies and even worse food", Dick stifled a yawn into his hand, sinking further into the couch and closing his eyes for a moment, the man needed sleep, Jason took a seat next to him on the couch, almost close enough for their shoulders to touch.

"What, booze and ladies aren't in anymore? No one told me. Someone should let Harley know as well, she needs to find a new job. No more parties in Gotham", Dick actually chuckled at the lame joke and Jason felt him move, so he could lay his head onto Jason's shoulder. The Red Hood went stiff for a moment, but he breathed out, relaxing, this wasn't anything new. And he got his alone time with Dick now!

"It's not too bad, the food was good. Remember to thank Alfred for it, you ate most of that batch of muffins right?" Jason rolled his eyes, but as there was sleepy smile on Dick's features, the man's eyes closed when he sneaked himself somehow around Jason's arm too, he couldn't but shake his head a bit.

"What can I say? I ain't about to throw those muffins into waste"

"You need to book a time for dentist Jay, you're bound to have cavities..."

"Does Batman provide dental care for his birds? Cause if he does I might be open to take a job back", Dick chuckled a bit again, yawning, rubbing his head against Jason's shoulder and snuggling better against him. Jason was sure he'd be asleep in less than five minutes, but Jason didn't really mind. Dick looked to be in desperate need for sleep, so if anything good came out of this party, at least the man would get some rest. Screw demon brat and his plans.

"Dentist Jason, first thing in the morning", Jason rolled his eyes, even though he knew the man couldn't see it; "yes yes mother dearest", this time he only got a smile in return.

"Thanks for this though, 't was a nice party, nice people", Jason detested hearing that, and this party was only the beginning he was sure, but he couldn't tell that to Dickie now could he?

"Don't mention it Dickiebird, have a sweet dreams now", as much as Jason hated to admit this was kind of nice, and his hand found a way to go and brush some hair off Dick's face, Dick's smiling sleepy face, which looked pretty nice to look at too. Red Hood did not look forward to more dates, to Dick having more dates with strangers, this was all a bad idea. Yeah nothing like healthy dosage of regrets made life worth living.


End file.
